4-(4-Methoxynaphthalen-1-yloxy)-1-nitrobenzene → 4-(4-Methoxy-naphthalen-1-yloxy)aniline

HRID 17716Notes

Reaction equation

HRID 17716 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)=[CH:5][CH:4]=1>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 669773744-(4-Methoxynaphthalen-1-yloxy)-1-nitrobenzene

Product 1

HCID 669774504-(4-Methoxy-naphthalen-1-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The nitro intermediate (10 mmol) obtained above was dissolved in EtOAc (50 mL) and hydrogenated in the presence of 10% Pd/C (360 mg) until completion according to General Procedure H, as indicated by TLC or HPLC. The reaction mixture was then filtered to remove the catalyst. The solvent was removed in vacuuo to afford the desired 4-(4-methoxy-naphthalen-1-yloxy)aniline, which was used directly for further transformation without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customto remove the catalyst
  3. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-8fe4de66f704498f9920a77fee9b4f5c
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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